First, make an honest assessment of whether or not you (a) are a "people person", or (b) can fake it for long enough for your subjects to really believe you are

First, make an honest assessment of whether or not you (a) are a "people person", or (b) can fake it for long enough for your subjects to really believe you are one. I'm not going to kid you: if you're a severe introvert who can't at least pretend to be open in a convincing way, then the majority of the work you'd need to do to get into the game is actually on your own comfort and skills in the social setting. If you're up to the game, or at least think you could be, then starting with a YouTube search for "Peter Hurley headshot" and watching the excerpts from "The Art Behind the Headshot" (they'll be at the Fstoppers channel) is a great place to start. Hurley's a salesman with an ego, and his clientelle are mostly actors looking for a different sort of headshot than the typical corporate client, but don't let any of that get in the way - the interaction tricks, etc., are still the same. Posing should seem like little offhand comments in the rest of the patter; the idea is to get rid of the obvious, gigantic and scary camera thing, and reminding the subject that the photo is important is going to kill that. Expect a low "keeper" rate, especially early on. (If you allow time for school pictures, you're going to get school pictures.) Once you've watched Hurley, you'll be able to judge others. Joe McNally's humble approach - like he's been given the privilege of taking the photo, no matter who's in front of the camera - also works well. Find someone who reminds you of who you'd like to be, and can be, behind the camera. But it's about reading the people and working with them as people that makes all of the difference.